Intra- and Intermolecular Oxa-Pictet–Spengler Cyclization Strategy for the Enantioselective Synthesis of Deoxy Analogues of (+)-Nanomycin A Methyl Ester, (+)-Eleutherin, (+)-Allo-Eleutherin, and (+)-Thysanone
✍ Scribed by Rajiv T. Sawant; Satish G. Jadhav; Suresh B. Waghmode
- Publisher
- John Wiley and Sons
- Year
- 2010
- Tongue
- English
- Weight
- 229 KB
- Volume
- 2010
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
Enantioselective synthesis of deoxy analogues of pyranonaphthoquinone antibiotics (+)‐nanomycin A methyl ester, (+)‐eleutherin, (+)‐allo‐eleutherin, and (+)‐thysanone was achieved in good overall yield with high enantio‐ and diastereoselectivity from the common intermediate (R)‐3‐(2,5‐dimethoxyphenyl)propane‐1,2‐diol. The intramolecular oxa‐Pictet–Spengler cyclization of 6‐aryl‐1,3‐dioxolone was developed for the first time and utilized in the enantioselective synthesis of (+)‐deoxynanomycin A methyl ester, whereas the intermolecular oxa‐Pictet–Spengler cyclization strategy was applied to the enantioselective synthesis of deoxy analogues of (+)‐eleutherin, (+)‐allo‐eleutherin, and (+)‐thysanone.